US5178792A - Macrocyclic compounds as component for ferroelectric liquid crystal mixtures - Google Patents

Macrocyclic compounds as component for ferroelectric liquid crystal mixtures Download PDF

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Publication number
US5178792A
US5178792A US07/683,263 US68326391A US5178792A US 5178792 A US5178792 A US 5178792A US 68326391 A US68326391 A US 68326391A US 5178792 A US5178792 A US 5178792A
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liquid crystal
crystal mixture
mixture
flc
ferroelectric liquid
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Takamasa Harada
Norbert Rosch
Peter Wegener
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Hoechst AG
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Hoechst AG
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Assigned to HOECHST AKTIENGESELLSCHAFT, D-6230 FRANKFURT AM MAIN 80, FEDERAL REPUBLIC OF GERMANY A CORP OF GERMANY reassignment HOECHST AKTIENGESELLSCHAFT, D-6230 FRANKFURT AM MAIN 80, FEDERAL REPUBLIC OF GERMANY A CORP OF GERMANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ROSCH, NORBERT, WEGENER, PETER, HARADA, TAKAMASA
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/582—Electrically active dopants, e.g. charge transfer agents
    • C09K19/584—Electrically active dopants, e.g. charge transfer agents having a condensed ring system; macrocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition

Definitions

  • the invention relates to the use of macrocyclic compounds in ferroelectric liquid crystal mixtures and the use of these mixtures in electrooptical switching and display elements.
  • Liquid crystal light valves are devices which change their optical transmission properties, for example because of electrical switching, in such a manner that transmitted (and, if appropriate, again reflected) light is intensity-modulated.
  • Examples are the known wristwatch and pocket calculator displays or liquid crystal displays in the areas of OA (office automation) or TV (television). However, they also include optical shutters, so-called “light shutters”, such as are used, for example, in copying machines, printers, welding goggles, polarized spectacles for three-dimensional viewing and the like. So-called “spatial light modulators” are also included in the application range of liquid-crystalline light valves (see Liquid Crystal Device Handbook, Nikkan Kogyo Shimbun, Tokyo, 1989; ISBN 4-526-02590-9C 3054 and articles quoted therein).
  • the structure of electrooptical switching and display elements is such that the FLC layer is enclosed on both sides by layers which conventionally contain, in the following order starting from the FLC layer, at least one electrically insulating layer, electrodes and an outer sheet (for example made of glass). Moreover they contain a polarizer, if they are operated in the "guest-host" or in the reflective mode, or two polarizers, if the birefringence mode is utilized.
  • Orientation layers together with a sufficiently small spacing of the outer sheets make the FLC molecules of the FLC mixture adopt a configuration in which the molecules are parallel to one another with respect to their longitudinal axes and the smectic planes are arranged perpendicular or inclined to the orientation layer.
  • the molecules as is known, have two equivalent orientations between which they can be switched by applying a pulsed electric field, i.e. FLC displays are capable of bistable switching.
  • the switching times are inversely proportional to the spontaneous polarization of the FLC mixture and are in the range of ⁇ s.
  • FLC displays In the non-addressed state they display an undesirable non-uniformity of the director (i.e. the preferred direction of the molecule), and thus one or more so-called twist states (M. A. Handschy, N. A. Clark, S. T. Lagerwall; Phys. Rev. Lett. 51, 471 (1983) M. Glogarova, J. Pavel; J. Phys. (France) 45, 143 (1984) N. Higi, T. Ouchi, H. Takezoe, A. Fukuda; Jap. J. Appl. Phys. 27, 8 (1988)).
  • this non-uniformity leads to a strong decline in the contrast in the display, in particular due to the fact that the opaque state becomes considerably lighter (gray dark state).
  • the appearance of the twist state is linked to a wavelength dispersion which can lead to distorted colors in the display.
  • the object of the present invention is to provide FLC mixtures which, in FLC displays, do not form twist states but lead to uniform states and thus to a high contrast.
  • a ferroelectric liquid crystal mixture composed of at least two components, which contains as one component at least one macrocyclic compound of the general formula (1) ##STR2## in which a, b, c, d, e, f, independently of one another, are an integer from zero to 4, a+b+c+d+e+f being greater than 7, and
  • R can be alkyl of 1 to 12 carbon atoms
  • R' can be alkyl of 1 to 12 carbon atoms, in which a --CH 2 -- group can be replaced by --O--, --COO--or --OCO--, phenyl or Cl, F or CN.
  • a ferroelectric liquid crystal mixture is used containing a macrocyclic compound of the formula (1), in which the symbols have the following meaning: a, b, c, d, e, f, R, R' are as described above, --B--, --C--, --E--, --F-- are a --CH 2 -- group and --A--, --D--, identical or different, are ##STR4##
  • macrocyclic compounds according to the formula (1) are used in which the symbols have the following meaning:
  • a, b, c, d, e, f independently of one another are an integer from zero to 3,
  • --B--, --C--, --E--, --F-- are a --CH 2 -- group --A--, --D--, identical or different, are ##STR5## in which R is alkyl of 1 to 12 carbon atoms and
  • R' is alkyl of 1 to 12 carbon atoms or phenyl.
  • the groups --A--, --D-- have the following meaning: ##STR6##
  • the mixture according to the invention contains 0.01 to 10 mol %, in particular 0.1 to 10 mol %, of the macrocyclic compound.
  • the liquid crystal mixtures comprise 2 to 20, preferably 2 to 15, components, of which at least one is a macrocylic compound.
  • the other components are preferably selected from the known compounds having nematic, cholesteric and/or tilted/ smectic phases, which include, for example, Schiff's bases, biphenyls, terphenyls, phenylcyclohexanes, cyclohexylbiphenyls, pyrimidines, cinnamic esters, cholesteric esters, various bridged polynuclear esters of p-alkylbenzoic acids having polar end groups.
  • the commercially available liquid crystal mixtures are present as mixtures of a wide range of components even before the compound(s) according to the invention is(are) added, at least one of which components being mesogenic, i.e. a compound which as a derivative or in a mixture with certain components shows a liquid crystal phase [i.e. is expected to form at least one enantiotropic (clearing temperature>melting temperature) or monotropic (clearing temperature ⁇ melting temperature) mesophase].
  • liquid crystal mixtures described can be advantageously incorporated in electrooptical switching and display devices.
  • the switching and display devices according to the invention contain, inter alia, the following components: a liquid-crystalline mixture according to the invention (containing a macrocyclic compound), support plates (e.g. made of glass or plastic), coated with transparent electrodes (two electrodes), at least one orientation layer, spacers, adhesive frame, polarizers and for color displays thin color filter films. Further possible components are antireflection, passivation, compensation and barrier coatings and electric non-linear elements, such as, for example, thin-film transistors (TFT) and metal/insulator/metal (MIM) elements.
  • TFT thin-film transistors
  • MIM metal/insulator/metal
  • FLC light valves switching devices which are driven by the multiplex process are preferred.
  • Liquid crystal cells which operate in the SSFLC technique ("surface stabilized ferroelectric liquid crystal") and in which the cell thickness (i.e. the spacing of the outer sheets) is 1 to 20 ⁇ m are particularly preferred.
  • the compounds according to the invention are advantageously used for the operation of an SSFLC display in the so-called "guest-host mode", in which the optical effect is not based on birefringence phenomena but on the anisotropic absorption of dichroic dyes which are dissolved in an FLC matrix.
  • the compounds according to the invention suppress the occurrence of twist states for various geometries of the smectic layers in the SSFLC cell (see, for example, H. R. Dubal, C. Escher, D. Ohlendorf; Proc. 6th Intl. Symp. on Electrets, Oxford, England (1988)). This is especially true of the so-called “virgin texture” in which the smectic layers are arranged at an angle ("chevron" geometry) and of the "bookshelf” or “quasi-bookshelf” geometry in which the smectic layers are arranged perpendicular to the glass plates (see Y. Sato et al., Jap. J. Appl. Phys. 28, 483 (1989)).
  • the use of the compounds according to the invention in this "bookshelf” geometry is particularly advantageous, since this not only leads to good dark states but also to high transmission of the bright state due to the large effective switching angle.
  • the compounds according to the invention facilitate in FLC mixtures the field-induced generation of a homogeneous "quasi-bookshelf" geometry (Y. Sato et al., Jap. J. Appl. Phys. 28, 483 (1989)).
  • Macrocyclic compounds in particular those of the general formula (1), can in general be prepared by the following methods:
  • the saturated lactone (2-oxacycloheptadecan-1-one) is obtained analogously as a wax-like light crystalline material.
  • the compound shown can be synthesized by methods known from the literature (see, for example, B. D. Mookherjee, R. W. Trenkle, R. R. Patel, J. Org. Chem. , 3266 (1971).
  • 0.1 ml of HCl (conc.) is added to a solution of 10 g of 8-cyclohexadecen-1-one in 25 ml of methyl orthoformate. After 12 hours, 0.1 g of benzenesulfonic acid is added and first methyl formate and then excess ortho ester are distilled off by slowly increasing the temperature.
  • the mixture is brought to a pH of 10 by adding 0.4 ml of sodium methoxide solution (30% in methanol), and the product is distilled off at 100° to 110° C./0.1 mbar; 8.1 g as a mixture of 1-methoxycyclohexa-1,7-diene and 1-methoxycyclohexa-1,8-diene, both as a cis/trans mixture.
  • the IR spectrum no longer shows the carbonyl band (1710 cm -1 ) of the starting material, but it shows the C ⁇ N band (1650 -1 ) of a hydrazone; in the 1 H NMR, a singlet appears at 2.4 ppm for the methyl group.
  • EXAMPLE 13 was prepared by the method of P. Rothemund, C. L. Gage, J. Am. Chem. Soc. 77, 3340 (1955); melting point: 294° C.
  • EXAMPLE 14 was prepared by the method of M. De Sousa-Hecely, A. J. Rest, J. Chem. Soc. Chem. Comm. 1981, 149; melting point: 241° C.
  • EXAMPLE 15 was prepared by the method of L. Mandolini, B. Masci, J. Org. Chem. 42, 2840 (1977); melting point: 56° C.
  • An LC basic mixture is prepared from the following 8 components (in mol %)
  • the mixture has the following phase transitions:
  • the LC mixture mentioned, the doping substances and the macrocyclic compounds mentioned in the examples are used to prepare the following working examples (FLC mixtures).
  • the switching angle, the transmission properties and the contrast in measurement cells (manufactured by E. H. C. Inc., Tokyo) which are filled with the mixtures mentioned are determined as the measure for suppressing twist states.
  • the FLC comparison mixture has the following composition (in mol %):
  • the switching angle (2 ⁇ eff ) is investigated for this comparison mixture and for an FLC mixture which in addition contains a macrocyclic compound from Example 6.
  • a measurement cell containing the corresponding FLC mixture is aligned under a polarizing microscope (equipped with revolving stage).
  • the switching angle of addressed cells can be determined by rotating the microscope stage.
  • the FLC mixture shows significantly improved properties, which is reflected in the corresponding measured results.
  • the effective switching angle (2 ⁇ eff ) is determined for each of the FLC mixtures containing the macrocyclic compounds from Examples 1, 3, 4 and 5.
  • the results show the significant improvement in the switching angle (and thus the contrast in the display) compared with the comparative example (without macrocyclic compound).

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
US07/683,263 1990-04-12 1991-04-10 Macrocyclic compounds as component for ferroelectric liquid crystal mixtures Expired - Fee Related US5178792A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4011804 1990-04-12
DE4011804A DE4011804A1 (de) 1990-04-12 1990-04-12 Verwendung von makrocyclischen verbindungen als komponente fuer ferroelektrische fluessigkristallmischungen

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US (1) US5178792A (enrdf_load_stackoverflow)
EP (1) EP0451822B1 (enrdf_load_stackoverflow)
JP (1) JPH04225090A (enrdf_load_stackoverflow)
KR (1) KR910018519A (enrdf_load_stackoverflow)
CN (1) CN1055754A (enrdf_load_stackoverflow)
AU (1) AU7428891A (enrdf_load_stackoverflow)
CA (1) CA2040268A1 (enrdf_load_stackoverflow)
CS (1) CS101591A3 (enrdf_load_stackoverflow)
DE (2) DE4011804A1 (enrdf_load_stackoverflow)
FI (1) FI911720L (enrdf_load_stackoverflow)
HU (1) HUT56868A (enrdf_load_stackoverflow)
IL (1) IL97816A0 (enrdf_load_stackoverflow)
NO (1) NO911433L (enrdf_load_stackoverflow)
PL (1) PL289848A1 (enrdf_load_stackoverflow)
PT (1) PT97341A (enrdf_load_stackoverflow)
TW (1) TW205066B (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5384168A (en) * 1990-04-21 1995-01-24 Hoechst Aktiengesellschaft Ferroelectric liquid-crystal display of high contrast and brightness
US5405552A (en) * 1992-08-11 1995-04-11 Hoechst Aktiengesellschaft Modified polysugar as the alignment layer for liquid-crystal displays
US5409635A (en) * 1991-01-15 1995-04-25 Hoechst Aktiengesellschaft Alignment layers containing cyclic structural elements
US5430564A (en) * 1990-06-14 1995-07-04 Hoechst Aktiengesellschaft Process for producing ferroelectric liquid-crystal cells with oleophilic additive employing heat and low pressure overlapped a short time
US5445762A (en) * 1991-08-21 1995-08-29 Hoechst Aktiengesellschaft Stabilized complex ligands and their use in liquid crystal displays
US5702639A (en) * 1989-12-01 1997-12-30 Hoechst Aktiengesellschaft Use of complex ligands for ions in ferroelectric liquid-crystal mixtures
US5938972A (en) * 1996-05-20 1999-08-17 Sony Corporation Liquid crystal composition, production thereof, and liquid crystal element made therewith
US6051639A (en) * 1996-04-01 2000-04-18 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Liquid crystal macrocycles

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05297376A (ja) * 1992-04-20 1993-11-12 Hoechst Japan Ltd 強誘電性液晶ディスプレイ素子
JPH05297375A (ja) * 1992-04-20 1993-11-12 Hoechst Japan Ltd 強誘電性液晶混合物およびこれを用いたディスプレイ素子

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2344617A1 (fr) * 1976-03-18 1977-10-14 Merck Patent Gmbh Dielectrique a cristaux liquides
US4367924A (en) * 1980-01-08 1983-01-11 Clark Noel A Chiral smectic C or H liquid crystal electro-optical device
EP0350842A2 (en) * 1988-07-11 1990-01-17 MONTEDISON S.p.A. Pyramidal liquid crystals
US4918217A (en) * 1987-07-21 1990-04-17 Montedison S.P.A. Macrocyclic tetramers having columnar tridimensional mesophases
WO1990015117A1 (en) * 1989-05-27 1990-12-13 Mitsubishi Kasei Corporation Liquid crystal composition and liquid crystal element
US5020881A (en) * 1988-01-26 1991-06-04 Canon Kabushiki Kaisha Light modulating device with optical switching unit of laminated insulating and conductive layers
DE3939697A1 (de) * 1989-12-01 1991-06-06 Hoechst Ag Verwendung von komplexliganden fuer ionen in ferroelektrischen fluessigkristallmischungen
WO1991008272A1 (de) * 1989-12-01 1991-06-13 Hoechst Aktiengesellschaft Verwendung von komplexliganden für ionen in ferroelektrischen flüssigkristallmischungen

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2344617A1 (fr) * 1976-03-18 1977-10-14 Merck Patent Gmbh Dielectrique a cristaux liquides
US4077900A (en) * 1976-03-18 1978-03-07 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline dielectric composition
US4367924A (en) * 1980-01-08 1983-01-11 Clark Noel A Chiral smectic C or H liquid crystal electro-optical device
US4918217A (en) * 1987-07-21 1990-04-17 Montedison S.P.A. Macrocyclic tetramers having columnar tridimensional mesophases
US5020881A (en) * 1988-01-26 1991-06-04 Canon Kabushiki Kaisha Light modulating device with optical switching unit of laminated insulating and conductive layers
EP0350842A2 (en) * 1988-07-11 1990-01-17 MONTEDISON S.p.A. Pyramidal liquid crystals
WO1990015117A1 (en) * 1989-05-27 1990-12-13 Mitsubishi Kasei Corporation Liquid crystal composition and liquid crystal element
DE3939697A1 (de) * 1989-12-01 1991-06-06 Hoechst Ag Verwendung von komplexliganden fuer ionen in ferroelektrischen fluessigkristallmischungen
WO1991008272A1 (de) * 1989-12-01 1991-06-13 Hoechst Aktiengesellschaft Verwendung von komplexliganden für ionen in ferroelektrischen flüssigkristallmischungen

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5702639A (en) * 1989-12-01 1997-12-30 Hoechst Aktiengesellschaft Use of complex ligands for ions in ferroelectric liquid-crystal mixtures
US5384168A (en) * 1990-04-21 1995-01-24 Hoechst Aktiengesellschaft Ferroelectric liquid-crystal display of high contrast and brightness
US5430564A (en) * 1990-06-14 1995-07-04 Hoechst Aktiengesellschaft Process for producing ferroelectric liquid-crystal cells with oleophilic additive employing heat and low pressure overlapped a short time
US5409635A (en) * 1991-01-15 1995-04-25 Hoechst Aktiengesellschaft Alignment layers containing cyclic structural elements
US5445762A (en) * 1991-08-21 1995-08-29 Hoechst Aktiengesellschaft Stabilized complex ligands and their use in liquid crystal displays
US5405552A (en) * 1992-08-11 1995-04-11 Hoechst Aktiengesellschaft Modified polysugar as the alignment layer for liquid-crystal displays
US6051639A (en) * 1996-04-01 2000-04-18 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Liquid crystal macrocycles
US5938972A (en) * 1996-05-20 1999-08-17 Sony Corporation Liquid crystal composition, production thereof, and liquid crystal element made therewith

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Publication number Publication date
HUT56868A (en) 1991-10-28
EP0451822A2 (de) 1991-10-16
FI911720A7 (fi) 1991-10-13
EP0451822A3 (en) 1992-03-18
NO911433D0 (no) 1991-04-11
IL97816A0 (en) 1992-06-21
PT97341A (pt) 1992-01-31
JPH04225090A (ja) 1992-08-14
CS101591A3 (en) 1992-05-13
CA2040268A1 (en) 1991-10-13
DE4011804A1 (de) 1991-10-24
NO911433L (no) 1991-10-14
DE59107399D1 (de) 1996-03-28
EP0451822B1 (de) 1996-02-14
AU7428891A (en) 1991-10-17
PL289848A1 (en) 1992-02-24
FI911720L (fi) 1991-10-13
TW205066B (enrdf_load_stackoverflow) 1993-05-01
KR910018519A (ko) 1991-11-30
FI911720A0 (fi) 1991-04-10
CN1055754A (zh) 1991-10-30

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